3-[(1S,6R)-3,4-Dimethyl-6-((1R,2R,3R,4R)-1,2,3,4,5-pentahydroxy-pentyl)-cyclohex-3-enyl]-propionic acid methyl ester | 374592-20-8

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-[(1S,6R)-3,4-Dimethyl-6-((1R,2R,3R,4R)-1,2,3,4,5-pentahydroxy-pentyl)-cyclohex-3-enyl]-propionic acid methyl ester
• CAS: 374592-20-8
• 化学式: C₁₇H₃₀O₇
• 分子量: 346.421
• InChiKey: WVKXOTGTSHKVRE-YCEVJDTHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.26
• 重原子数：
  24.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  127.45
• 氢给体数：
  5.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  3-[(1S,6R)-3,4-Dimethyl-6-((1R,2R,3R,4R)-1,2,3,4,5-pentahydroxy-pentyl)-cyclohex-3-enyl]-propionic acid methyl ester 在 sodium periodate 作用下， 生成 3-((1S,6R)-6-Formyl-3,4-dimethyl-cyclohex-3-enyl)-propionic acid methyl ester
  参考文献：
  名称：

  Stereoselective denitrohydrogenation reactions of 4-alkyl-5-glyco-4-nitrocyclohex-1-enes

  摘要：

  The denitrohydrogenation of chiral 4-alkyl-5-glyco-4-nitrocyclohex-1-enes (1 and 3) with tri-n-butyltin hydride and azobisisobutironitrile proceeded in a completely stereoselective way. In each case. the hydrogen atom provided by tri-n-butyltin hydride adds to a free radical intermediate in a trans mode to the adjacent, sterically demanding, sugar side-chain. Attempts to perform denitroalkylation reactions of 1a, 3a or 8 with electron-deficient alkenes yielded only denitrohydrogenated products. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00304-4
• 作为产物：
  描述：

  3-[(1S,6R)-3,4-Dimethyl-6-((1R,2R,3R,4R)-1,2,3,4,5-pentaacetoxy-pentyl)-cyclohex-3-enyl]-propionic acid methyl ester 在 sodium methylate 作用下， 以64%的产率得到3-[(1S,6R)-3,4-Dimethyl-6-((1R,2R,3R,4R)-1,2,3,4,5-pentahydroxy-pentyl)-cyclohex-3-enyl]-propionic acid methyl ester
  参考文献：
  名称：

  Stereoselective denitrohydrogenation reactions of 4-alkyl-5-glyco-4-nitrocyclohex-1-enes

  摘要：

  The denitrohydrogenation of chiral 4-alkyl-5-glyco-4-nitrocyclohex-1-enes (1 and 3) with tri-n-butyltin hydride and azobisisobutironitrile proceeded in a completely stereoselective way. In each case. the hydrogen atom provided by tri-n-butyltin hydride adds to a free radical intermediate in a trans mode to the adjacent, sterically demanding, sugar side-chain. Attempts to perform denitroalkylation reactions of 1a, 3a or 8 with electron-deficient alkenes yielded only denitrohydrogenated products. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00304-4